A route enabling the synthesis of the stereo-triad of rishirilide B (1) from 2-hydroxy-3-methylnaphthalene-1,4-dione, is reported. Key transformations include the regioselective 1,2-Grignard addition to a tautomeric mixture of o- and p-quinones, regioselective carbamoylation of a tautomeric mixture, and a synopsis of the methods explored to convert various terminal vinyl ethers into the corresponding carboxylic acid by cleavage.
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http://dx.doi.org/10.1055/s-2006-950188 | DOI Listing |
Langmuir
January 2025
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Inclusion complexation of the sunscreen ingredient avobenzone (AVB) with β-cyclodextrin (β-CD) was investigated to improve its aqueous solubility and photostability; another ultraviolet (UV) filter, oxybenzone (OXB), and the phytochemical antioxidant curcumin (CUR) served as a comparison. In this study, the 1-octanol/water partition coefficients, acid dissociation constants, phase-solubility diagrams with β-CD, and ultraviolet-visible (UV-vis) spectral changes induced by UVA1 (365 nm) irradiation were evaluated. β-CD at concentrations 50-100 times that of AVB most effectively protected the photostability of AVB.
View Article and Find Full Text PDFInorg Chem
October 2024
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, Zaragoza 50009, Spain.
The reaction of the 11-vertex rhodathiaborane [8,8,8-(H)(PPh)-3-(NCH)--7,8-RhSBH] () with 1,2-bis(diphenylphosphine)benzene (dppbz) and ()-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (binap) affords [1,1-(η-dppbz)-3-(NCH)--1,2-RhSBH] () and [1,1-(η-binap)-3-(NCH)--1,2-RhSBH] (). These 11-vertex -rhodathiaborane chelates result from PPh ligand substitution at the rhodium center and a -to- structural cluster transformation driven by H loss. Treating compounds and with triflic acid (TfOH) leads to the formation of cationic clusters and .
View Article and Find Full Text PDFDrug Test Anal
August 2024
Key Laboratory of Drug Monitoring and Control, Drug Intelligence and Forensic Center, Ministry of Public Security, Beijing, China.
The effective implementation of drug precursor legislation has driven the innovation and design of new alternative substances. The application of 1,3-dicarbonyl precursors as alternative precursors for the synthesis of 1-phenyl-2-propanone (P2P) and 3,4-methylenedioxyphenyl-2-propanone (MDP2P) has created new challenges to legal control. Their 1,3-dicarbonyl structure allows the precursors to exist as an equilibrium mixture of the tautomeric diketo and keto-enolic forms during the nuclear magnetic resonance (NMR) analysis.
View Article and Find Full Text PDFNature
August 2024
College of Physics, Jilin University, Changchun, China.
Org Biomol Chem
July 2024
Department of Chemistry, National Dong Hwa University, Hualien 97401, Taiwan, R.O.C..
The arene cyclopropanation between diazo compounds and benzene is well known to produce a tautomeric mixture of norcaradiene and cycloheptatriene in favour of the latter species. Nevertheless, previous studies have suggested that the initially formed norcaradiene can be stabilized by a C-7 cyano group with prevention of its 6π-electrocyclic ring opening. According to this feature, a synthetic route to functionalized cyclohexadienes has been designed using α-cyanodiazoacetates and α-diazo-β-ketonitriles as the starting materials, respectively.
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